NPASS Compound

Structure

NPC15956 OpenBabel07101719252D 36 39 0 0 1 0 0 0 0 0999 V2000 -1.6473 0.5352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7891 -0.0999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8187 -5.0486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3546 -5.0486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3546 -4.0486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2891 0.7661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7891 1.6321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4886 -5.5486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2206 -2.5486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0866 -4.0486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7891 -0.0999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6254 -0.3273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6691 0.7431 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2206 -3.5486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7891 -0.0999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0866 -2.0486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2946 -1.0705 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7891 1.6321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2891 0.7661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9527 -3.5486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3601 1.6942 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6180 1.9021 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2872 1.1590 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2891 -0.9659 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9527 -2.5486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 0.2079 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4886 -6.5486 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2891 2.4982 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0292 2.4373 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9271 2.8532 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2653 1.3669 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2891 0.7661 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8187 -4.0486 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6473 -0.5352 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6958 -1.8795 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 32 1 0 0 0 0 3 33 1 0 0 0 0 4 5 1 0 0 0 0 4 8 1 0 0 0 0 5 14 1 0 0 0 0 6 7 2 0 0 0 0 6 15 1 0 0 0 0 7 18 1 0 0 0 0 8 27 1 0 0 0 0 9 14 2 0 0 0 0 9 16 1 0 0 0 0 10 14 1 0 0 0 0 10 20 2 0 0 0 0 11 15 2 0 0 0 0 11 19 1 0 0 0 0 12 34 1 0 0 0 0 13 1 1 1 0 0 0 13 21 1 0 0 0 0 13 35 1 0 0 0 0 16 17 1 0 0 0 0 16 25 2 0 0 0 0 17 12 1 6 0 0 0 17 24 1 0 0 0 0 18 19 2 0 0 0 0 18 28 1 0 0 0 0 19 32 1 0 0 0 0 20 25 1 0 0 0 0 20 33 1 0 0 0 0 21 22 1 0 0 0 0 21 29 1 6 0 0 0 22 23 1 0 0 0 0 22 30 1 1 0 0 0 23 26 1 0 0 0 0 23 31 1 1 0 0 0 24 15 1 1 0 0 0 24 36 1 0 0 0 0 25 36 1 0 0 0 0 26 34 1 6 0 0 0 26 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	506.22
Volume:	496.11
LogP:	1.691
LogD:	1.524
LogS:	-3.472
# Rotatable Bonds:	9
TPSA:	147.3
# H-Bond Aceptor:	10
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.338
Synthetic Accessibility Score:	4.328
Fsp3:	0.538
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.996
MDCK Permeability:	1.7263249901589006e-05
Pgp-inhibitor:	0.034
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.049
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.244

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.198
Plasma Protein Binding (PPB):	74.6639633178711%
Volume Distribution (VD):	0.449
Pgp-substrate:	12.806716918945312%

ADMET: Metabolism

CYP1A2-inhibitor:	0.029
CYP1A2-substrate:	0.629
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.781
CYP2C9-inhibitor:	0.039
CYP2C9-substrate:	0.422
CYP2D6-inhibitor:	0.023
CYP2D6-substrate:	0.238
CYP3A4-inhibitor:	0.167
CYP3A4-substrate:	0.603

ADMET: Excretion

Clearance (CL):	6.828
Half-life (T1/2):	0.504

ADMET: Toxicity

hERG Blockers:	0.267
Human Hepatotoxicity (H-HT):	0.218
Drug-inuced Liver Injury (DILI):	0.72
AMES Toxicity:	0.475
Rat Oral Acute Toxicity:	0.06
Maximum Recommended Daily Dose:	0.101
Skin Sensitization:	0.948
Carcinogencity:	0.05
Eye Corrosion:	0.003
Eye Irritation:	0.033
Respiratory Toxicity:	0.643

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC15956

Natural Product ID:	NPC15956
*Common Name:**	OZOQXURHSVUEDM-FNMKIYJNSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	OZOQXURHSVUEDM-FNMKIYJNSA-N
Standard InCHI:	InChI=1S/C26H34O10/c1-13-21(29)22(30)23(31)26(35-13)34-12-17-16-9-14(5-4-8-27)10-20(33-3)25(16)36-24(17)15-6-7-18(28)19(11-15)32-2/h6-7,9-11,13,17,21-24,26-31H,4-5,8,12H2,1-3H3/t13-,17-,21-,22+,23+,24+,26+/m0/s1
SMILES:	C[C@H]1[C@@H]([C@H]([C@H]([C@H](OC[C@H]2c3cc(CCCO)cc(c3O[C@@H]2c2ccc(c(c2)OC)O)OC)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581701
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14600382]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[25894905]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[28358502]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	4
Others	2

Activity Type	# Activity
Cell Line	5
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT76	Cell Line	C6	Rattus norvegicus	Activity	=	102.88	%	PMID[466198]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	IC50	>	10000.0	nM	PMID[466198]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	>	10000.0	nM	PMID[466198]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[466198]
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	>	10000.0	nM	PMID[466198]
NPT27	Others	Unspecified		Activity	=	97.4	%	PMID[466198]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC15956 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	423
0.1-0.2	1485
0.2-0.3	3716
0.3-0.4	9493
0.4-0.5	9049
0.5-0.6	4663
0.6-0.7	7926
0.7-0.8	4630
0.8-0.85	877
0.85-0.9	350
0.9-0.95	66
0.95-1	19

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC114505
1.0	High Similarity	NPC275284
1.0	High Similarity	NPC193473
1.0	High Similarity	NPC213074
1.0	High Similarity	NPC31325
1.0	High Similarity	NPC224674
0.9856	High Similarity	NPC476301
0.9856	High Similarity	NPC43508
0.9789	High Similarity	NPC98624
0.9784	High Similarity	NPC471667
0.9784	High Similarity	NPC79429
0.9784	High Similarity	NPC217635
0.9712	High Similarity	NPC185307
0.9712	High Similarity	NPC470950
0.965	High Similarity	NPC472710
0.965	High Similarity	NPC472709
0.9643	High Similarity	NPC283995
0.9643	High Similarity	NPC470235
0.9643	High Similarity	NPC129417
0.964	High Similarity	NPC476356
0.964	High Similarity	NPC253878
0.9574	High Similarity	NPC22150
0.9574	High Similarity	NPC38041
0.9574	High Similarity	NPC279298
0.9571	High Similarity	NPC46092
0.9568	High Similarity	NPC471414
0.9568	High Similarity	NPC472711
0.951	High Similarity	NPC270751
0.9507	High Similarity	NPC112861
0.9441	High Similarity	NPC39657
0.9437	High Similarity	NPC18979
0.9433	High Similarity	NPC477898
0.9392	High Similarity	NPC228357
0.9366	High Similarity	NPC84181
0.9362	High Similarity	NPC246947
0.9353	High Similarity	NPC470413
0.9353	High Similarity	NPC138738
0.931	High Similarity	NPC51328
0.931	High Similarity	NPC44452
0.931	High Similarity	NPC55158
0.931	High Similarity	NPC286235
0.9301	High Similarity	NPC475096
0.9281	High Similarity	NPC10737
0.9281	High Similarity	NPC29799
0.9281	High Similarity	NPC177035
0.9281	High Similarity	NPC52277
0.9281	High Similarity	NPC263367
0.9281	High Similarity	NPC177160
0.9281	High Similarity	NPC477939
0.9281	High Similarity	NPC199459
0.9281	High Similarity	NPC54743
0.9281	High Similarity	NPC209985
0.9281	High Similarity	NPC156502
0.9267	High Similarity	NPC478269
0.9252	High Similarity	NPC302610
0.9247	High Similarity	NPC475224
0.9241	High Similarity	NPC248132
0.9241	High Similarity	NPC130449
0.9236	High Similarity	NPC99515
0.9236	High Similarity	NPC190714
0.9231	High Similarity	NPC164183
0.9231	High Similarity	NPC472713
0.9231	High Similarity	NPC187774
0.9231	High Similarity	NPC473046
0.9231	High Similarity	NPC472712
0.9231	High Similarity	NPC471063
0.9231	High Similarity	NPC118385
0.922	High Similarity	NPC106944
0.9209	High Similarity	NPC101624
0.9209	High Similarity	NPC184938
0.9172	High Similarity	NPC227902
0.9167	High Similarity	NPC286245
0.9167	High Similarity	NPC469586
0.9167	High Similarity	NPC272619
0.9161	High Similarity	NPC113680
0.9161	High Similarity	NPC278961
0.9149	High Similarity	NPC156376
0.9145	High Similarity	NPC478267
0.9137	High Similarity	NPC49603
0.9137	High Similarity	NPC187616
0.9137	High Similarity	NPC193026
0.9137	High Similarity	NPC476411
0.9137	High Similarity	NPC187194
0.9122	High Similarity	NPC474442
0.9116	High Similarity	NPC183380
0.911	High Similarity	NPC175976
0.9103	High Similarity	NPC125755
0.9103	High Similarity	NPC276753
0.9103	High Similarity	NPC260397
0.9103	High Similarity	NPC205796
0.9097	High Similarity	NPC471065
0.9097	High Similarity	NPC253015
0.9097	High Similarity	NPC25292
0.9097	High Similarity	NPC473045
0.9091	High Similarity	NPC472714
0.9091	High Similarity	NPC189115
0.9091	High Similarity	NPC475084
0.9091	High Similarity	NPC469559
0.9091	High Similarity	NPC131971
0.9091	High Similarity	NPC5262
0.9091	High Similarity	NPC302506
0.9078	High Similarity	NPC304152
0.9071	High Similarity	NPC79957
0.9065	High Similarity	NPC26394
0.906	High Similarity	NPC61604
0.906	High Similarity	NPC245615
0.906	High Similarity	NPC299706
0.906	High Similarity	NPC115466
0.9034	High Similarity	NPC180953
0.9034	High Similarity	NPC161700
0.9034	High Similarity	NPC277867
0.9034	High Similarity	NPC307466
0.9028	High Similarity	NPC81638
0.9028	High Similarity	NPC473044
0.9021	High Similarity	NPC263261
0.9021	High Similarity	NPC469661
0.9021	High Similarity	NPC471908
0.9021	High Similarity	NPC87725
0.9007	High Similarity	NPC77861
0.9	High Similarity	NPC35731
0.9	High Similarity	NPC470881
0.9	High Similarity	NPC478085
0.9	High Similarity	NPC159922
0.8993	High Similarity	NPC471505
0.8993	High Similarity	NPC106739
0.8993	High Similarity	NPC230219
0.8993	High Similarity	NPC21902
0.8986	High Similarity	NPC214326
0.8986	High Similarity	NPC469706
0.8986	High Similarity	NPC9933
0.8986	High Similarity	NPC260781
0.8986	High Similarity	NPC218041
0.8986	High Similarity	NPC182368
0.8986	High Similarity	NPC469707
0.8986	High Similarity	NPC145979
0.8986	High Similarity	NPC185955
0.8986	High Similarity	NPC225815
0.898	High Similarity	NPC474940
0.898	High Similarity	NPC303013
0.898	High Similarity	NPC130959
0.898	High Similarity	NPC166584
0.898	High Similarity	NPC304048
0.898	High Similarity	NPC301961
0.898	High Similarity	NPC71726
0.898	High Similarity	NPC226153
0.898	High Similarity	NPC159697
0.898	High Similarity	NPC474795
0.8966	High Similarity	NPC133251
0.8966	High Similarity	NPC45257
0.8966	High Similarity	NPC179521
0.8966	High Similarity	NPC138227
0.8966	High Similarity	NPC76176
0.8966	High Similarity	NPC12641
0.8966	High Similarity	NPC93323
0.8966	High Similarity	NPC280092
0.8966	High Similarity	NPC469313
0.8966	High Similarity	NPC168579
0.8966	High Similarity	NPC63879
0.8958	High Similarity	NPC41782
0.8958	High Similarity	NPC60249
0.8958	High Similarity	NPC48309
0.8951	High Similarity	NPC184797
0.8951	High Similarity	NPC309124
0.8936	High Similarity	NPC135777
0.8936	High Similarity	NPC142547
0.8933	High Similarity	NPC200645
0.8933	High Similarity	NPC475227
0.8933	High Similarity	NPC106669
0.8929	High Similarity	NPC6836
0.8929	High Similarity	NPC25821
0.8921	High Similarity	NPC248307
0.8921	High Similarity	NPC65942
0.8921	High Similarity	NPC476345
0.8912	High Similarity	NPC15538
0.8912	High Similarity	NPC473480
0.8904	High Similarity	NPC163898
0.8904	High Similarity	NPC181615
0.8897	High Similarity	NPC265154
0.8897	High Similarity	NPC47633
0.8897	High Similarity	NPC252169
0.8897	High Similarity	NPC37793
0.8897	High Similarity	NPC102044
0.8897	High Similarity	NPC85264
0.8889	High Similarity	NPC241600
0.8889	High Similarity	NPC76871
0.8889	High Similarity	NPC173726
0.8882	High Similarity	NPC163635
0.8882	High Similarity	NPC11411
0.8881	High Similarity	NPC88640
0.8881	High Similarity	NPC232164
0.8881	High Similarity	NPC473739
0.8881	High Similarity	NPC212770
0.8881	High Similarity	NPC70682
0.8881	High Similarity	NPC236306
0.8881	High Similarity	NPC292487
0.8881	High Similarity	NPC193666
0.8881	High Similarity	NPC260741
0.8881	High Similarity	NPC98777
0.8881	High Similarity	NPC123526
0.8867	High Similarity	NPC59692

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC15956 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	344
0.1-0.2	819
0.2-0.3	1767
0.3-0.4	2776
0.4-0.5	1751
0.5-0.6	970
0.6-0.7	597
0.7-0.8	119
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8759	High Similarity	NPD6674	Discontinued
0.8462	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD1613	Approved
0.8272	Intermediate Similarity	NPD7228	Approved
0.8252	Intermediate Similarity	NPD3027	Phase 3
0.8243	Intermediate Similarity	NPD7266	Discontinued
0.8182	Intermediate Similarity	NPD1653	Approved
0.8182	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD6234	Discontinued
0.8112	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8112	Intermediate Similarity	NPD2861	Phase 2
0.8089	Intermediate Similarity	NPD37	Approved
0.8071	Intermediate Similarity	NPD1091	Approved
0.8061	Intermediate Similarity	NPD7074	Phase 3
0.805	Intermediate Similarity	NPD4965	Approved
0.805	Intermediate Similarity	NPD4966	Approved
0.805	Intermediate Similarity	NPD4967	Phase 2
0.8049	Intermediate Similarity	NPD3818	Discontinued
0.8	Intermediate Similarity	NPD7054	Approved
0.7974	Intermediate Similarity	NPD5058	Phase 3
0.7963	Intermediate Similarity	NPD7199	Phase 2
0.7952	Intermediate Similarity	NPD7472	Approved
0.7945	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD3705	Approved
0.7925	Intermediate Similarity	NPD8455	Phase 2
0.7895	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD4060	Phase 1
0.7808	Intermediate Similarity	NPD4908	Phase 1
0.7758	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD7240	Approved
0.7751	Intermediate Similarity	NPD6559	Discontinued
0.7751	Intermediate Similarity	NPD7251	Discontinued
0.773	Intermediate Similarity	NPD1357	Approved
0.7718	Intermediate Similarity	NPD3620	Phase 2
0.7718	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD7808	Phase 3
0.7702	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6797	Phase 2
0.7692	Intermediate Similarity	NPD1610	Phase 2
0.7674	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD8651	Approved
0.7647	Intermediate Similarity	NPD7685	Pre-registration
0.764	Intermediate Similarity	NPD1934	Approved
0.7632	Intermediate Similarity	NPD5588	Approved
0.7602	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD4538	Approved
0.7566	Intermediate Similarity	NPD4536	Approved
0.7566	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD5283	Phase 1
0.7552	Intermediate Similarity	NPD5126	Approved
0.7552	Intermediate Similarity	NPD5125	Phase 3
0.7532	Intermediate Similarity	NPD5763	Approved
0.7532	Intermediate Similarity	NPD5762	Approved
0.7517	Intermediate Similarity	NPD4625	Phase 3
0.75	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6166	Phase 2
0.7485	Intermediate Similarity	NPD2978	Approved
0.7485	Intermediate Similarity	NPD2977	Approved
0.7457	Intermediate Similarity	NPD8312	Approved
0.7457	Intermediate Similarity	NPD8313	Approved
0.7451	Intermediate Similarity	NPD7097	Phase 1
0.7447	Intermediate Similarity	NPD7157	Approved
0.7434	Intermediate Similarity	NPD6355	Discontinued
0.7434	Intermediate Similarity	NPD5735	Approved
0.741	Intermediate Similarity	NPD228	Approved
0.7403	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD4108	Discontinued
0.7403	Intermediate Similarity	NPD5960	Phase 3
0.7396	Intermediate Similarity	NPD2489	Approved
0.7396	Intermediate Similarity	NPD27	Approved
0.7389	Intermediate Similarity	NPD6331	Phase 2
0.7368	Intermediate Similarity	NPD5844	Phase 1
0.7365	Intermediate Similarity	NPD5494	Approved
0.7357	Intermediate Similarity	NPD7843	Approved
0.7356	Intermediate Similarity	NPD7313	Approved
0.7356	Intermediate Similarity	NPD7311	Approved
0.7356	Intermediate Similarity	NPD7312	Approved
0.7356	Intermediate Similarity	NPD7310	Approved
0.7349	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD4749	Approved
0.7337	Intermediate Similarity	NPD2969	Approved
0.7337	Intermediate Similarity	NPD7680	Approved
0.7337	Intermediate Similarity	NPD2970	Approved
0.7324	Intermediate Similarity	NPD6671	Approved
0.7321	Intermediate Similarity	NPD8127	Discontinued
0.7314	Intermediate Similarity	NPD7309	Approved
0.7308	Intermediate Similarity	NPD1375	Discontinued
0.7308	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6696	Suspended
0.7292	Intermediate Similarity	NPD1548	Phase 1
0.7289	Intermediate Similarity	NPD3882	Suspended
0.7288	Intermediate Similarity	NPD7906	Approved
0.7278	Intermediate Similarity	NPD3051	Approved
0.7273	Intermediate Similarity	NPD2801	Approved
0.7267	Intermediate Similarity	NPD3018	Phase 2
0.7266	Intermediate Similarity	NPD3022	Approved
0.7266	Intermediate Similarity	NPD3021	Approved
0.7255	Intermediate Similarity	NPD1558	Phase 1
0.7247	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD7075	Discontinued
0.7232	Intermediate Similarity	NPD4663	Approved
0.723	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD5177	Phase 3
0.7208	Intermediate Similarity	NPD5124	Phase 1
0.7208	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6004	Phase 3
0.7197	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6002	Phase 3
0.7197	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6005	Phase 3
0.7195	Intermediate Similarity	NPD4380	Phase 2
0.7194	Intermediate Similarity	NPD2684	Approved
0.7179	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6071	Discontinued
0.7171	Intermediate Similarity	NPD7095	Approved
0.717	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD4110	Phase 3
0.7161	Intermediate Similarity	NPD6653	Approved
0.7159	Intermediate Similarity	NPD4577	Approved
0.7159	Intermediate Similarity	NPD4578	Approved
0.7152	Intermediate Similarity	NPD2424	Discontinued
0.7151	Intermediate Similarity	NPD7473	Discontinued
0.7143	Intermediate Similarity	NPD4140	Approved
0.7126	Intermediate Similarity	NPD3817	Phase 2
0.7126	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD2563	Approved
0.7126	Intermediate Similarity	NPD2560	Approved
0.7125	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD2677	Approved
0.7124	Intermediate Similarity	NPD6798	Discontinued
0.7122	Intermediate Similarity	NPD290	Approved
0.7117	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD5327	Phase 3
0.7114	Intermediate Similarity	NPD2982	Phase 2
0.7114	Intermediate Similarity	NPD2983	Phase 2
0.7107	Intermediate Similarity	NPD4236	Phase 3
0.7107	Intermediate Similarity	NPD4237	Approved
0.7099	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6842	Approved
0.7095	Intermediate Similarity	NPD6841	Approved
0.7095	Intermediate Similarity	NPD6843	Phase 3
0.7086	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD6666	Approved
0.7081	Intermediate Similarity	NPD6667	Approved
0.7076	Intermediate Similarity	NPD3787	Discontinued
0.7076	Intermediate Similarity	NPD6232	Discontinued
0.7072	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD7033	Discontinued
0.7066	Intermediate Similarity	NPD5772	Approved
0.7066	Intermediate Similarity	NPD1465	Phase 2
0.7066	Intermediate Similarity	NPD5773	Approved
0.7066	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD7819	Suspended
0.7063	Intermediate Similarity	NPD4628	Phase 3
0.7063	Intermediate Similarity	NPD4535	Phase 3
0.7055	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD2981	Phase 2
0.7037	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD1511	Approved
0.7037	Intermediate Similarity	NPD7041	Phase 2
0.703	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD3094	Phase 2
0.7019	Intermediate Similarity	NPD6190	Approved
0.7013	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1652	Phase 2
0.7	Intermediate Similarity	NPD3060	Approved
0.6994	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD7028	Phase 2
0.6977	Remote Similarity	NPD7229	Phase 3
0.6975	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD6584	Phase 3
0.6968	Remote Similarity	NPD6233	Phase 2
0.6964	Remote Similarity	NPD5929	Approved
0.6959	Remote Similarity	NPD4666	Phase 3
0.6959	Remote Similarity	NPD5846	Approved
0.6959	Remote Similarity	NPD6516	Phase 2
0.6957	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD1512	Approved
0.6951	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD52	Approved
0.6951	Remote Similarity	NPD7526	Approved
0.6946	Remote Similarity	NPD6072	Discontinued
0.6943	Remote Similarity	NPD6353	Approved
0.6933	Remote Similarity	NPD1774	Approved
0.6928	Remote Similarity	NPD7458	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data